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Meester was born in Fort Worth, Texas, to Constance Lynn (née Haas) and Douglas Jay Meester.[2][3] Her father is a real estate broker; her mother is a writer.[4] She has two brothers; an older brother, Douglas Logan Meester (born 1983), and a younger brother, Alexander "Lex" Meester (born 1994). At the time of her birth, Meester's parents were serving time in a federal prison for their involvement in a drug ring that smuggled marijuana from Jamaica to the United States.[5] Constance was able to give birth to Leighton in a hospital and nurse her for three months in a halfway house, before returning to prison to complete her sentence.[2][3] Her paternal grandparents cared for Meester during this period. She has maintained that her parents gave her a normal upbringing and, despite their criminal past, has stated, "It made me realize that you can't judge anyone—especially your parents—for what they've done in their past, because people change."[6] She grew up in Marco Island, Florida, where she participated in productions at a local playhouse.[7] Her parents separated in 1992.[8]

In 2006, Meester appeared in two films, Flourish and Inside. She also guest starred in an episode of Numbers and appeared in two episodes of House as Ali Johnson, a teenager who has a crush on Gregory House.[7] She then had guest roles on CSI: Miami[14] and Shark, and portrayed the female lead in the horror film Drive-Thru, for which she recorded the song "Inside the Black".[15] Meester was cast as identical twin sisters Kayla and Kelly Rhodes in the ABC crime-drama series Secrets of a Small Town,[16] but the network decided not to forward the series.[17]

In 2007, Meester was cast in The CW's teen drama series Gossip Girl as Blair Waldorf, based on the book series of the same name by Cecily von Ziegesar. She first auditioned for the role of Serena van der Woodsen, but told the producers that she could better play Blair. However, it was important that Serena was blonde and Blair was brunette, so Meester dyed her hair brown for the role.[18] Her performance was the most critically acclaimed of the show, with Blair being cited as the series' breakout character. She also garnered media attention for her wardrobe on the show.[3][19] The series ended after six seasons and 120 episodes.[20] Meester later starred in the television film The Haunting of Sorority Row,[21] and had a role in the ensemble comedy-drama film Remember the Daze.[22] In 2008, she appeared in the horror-thriller film Killer Movie and reprised her role in Entourage singing with Tony Bennett in the episode.[23] That same year, she was a spokesperson for Sunsilk's Life Can't Wait campaign to motivate women to pursue their dreams,[24] and collaborated with Safe Horizon to raise awareness about domestic violence.[25]

Her second single, "Your Love's a Drug", was digitally released on March 30, 2010,[35] and she is also featured on Stephen Jerzak's song "She Said".[36][37] Meester did a duet with DJ Clinton Sparks on "Front Cut", which appeared on the internet in February 2011.[38][39]Lil Wayne worked with her on an unreleased song titled "Make It Rain"[40] and Jesse McCartney wrote another song.[41] The album, produced by Polow Da Don, Harvey Mason Jr., and Spencer Nezey, which Meester began working on in March 2009, was initially projected to be released in fall 2009,[23][42] but was later delayed to early 2010.[43] It was pushed back again to late 2010,[44] and was ultimately shelved.

In 2010, Meester signed on to be the spokesperson for Herbal Essences hair products.[51][52] In the same year, she took part in Bulgari's humanitarian efforts for the Save the Children organization with Isabella Rossellini and Maribel Verdú.[53] She next fronted a beauty campaign for Korean brand eSpoir.[54]Vera Wang selected her to be the face of the fragrance Lovestruck in 2011, stating that Meester's "beauty, talent and spirit will inspire all the young women that I hope will enjoy this passionate, new young fragrance."[55] The next year, Meester shot a campaign for the followup fragrance, Lovestruck Floral Rush.[56] Italian fashion house Missoni named Meester the face of their spring/summer 2011 campaign.[57]

Meester next starred in the thriller film The Roommate as Rebecca Evans, an obsessive, bipolar woman.[58] Though the film received mainly negative reviews, Meester's portrayal was praised. Entertainment Weekly found she was the only one to bring "the slightest trace of something fascinating to her role,"[59] while Los Angeles Times wrote, "[Meester's] performance often has the feeling of a sports car in neutral. When she punches it for quick changes of tone from manic to wounded or around the bend, she shows how much more she is capable of."[60] In the teen comedy film Monte Carlo, Meester portrayed Meg Kelly, Selena Gomez's stepsister and Katie Cassidy's friend.[61]Movieline noted, "As in Country Strong, Meester's crack timing and irresistible poignancy illuminate a part that would leave other actresses simpering themselves off the screen."[62] Her final film of the year, The Oranges, opposite Hugh Laurie and Adam Brody, premiered at the Toronto International Film Festival.[63] Meester's performance was again met with positive reviews, with the San Francisco Chronicle writing that she "succeeds in embodying all that is alluring and alarming about a 24-year-old woman."[64]

In April 2012, Meester announced via Twitter a five-city tour with Check in the Dark, which started on May 29 and ended on June 4, 2012.[65] Reflecting on her past pop collaborations, she said she "loved" them, but that folk music was "a lot closer to [her] heart."[66] In May 2012, she endorsed the Philippine clothing brand Penshoppe's campaign All Stars.[67] In June, Meester said she and the band had recorded all the songs for an album that served as a demo.[68]

On September 9, 2014, it was announced her debut album, Heartstrings, would be released independently through her own label, Hotly Wanting, on October 28, 2014. With its style compared to ethereal singer-songwriters such as Tori Amos and Joni Mitchell, the nine-song LP was written by Meester and produced by Jeff Trott.[84][85] The music video for the eponymous title track "Heartstrings" was released on October 29, 2014.[86]

In 2015, Meester embarked on a tour to support the album, which began on January 6 in Los Angeles, California and ended on March 2 in San Francisco, California.[87] Later that year, she appeared in advertisements for the Malaysian fashion brand Jimmy Choo.[88] Meester was one of the 100 celebrity narrators featured in the documentary Unity, which had a limited theatrical release.[89] In March 2016, she was cast in Fox's comedy series Making History as Deborah Revere, a colonial woman from 1775 and the daughter of American artisan Paul Revere.[90] The series was cancelled after one season of nine episodes.[91] Meester had a guest role on The Last Man on Earth.[92]

In July 2011, Meester and her mother, Constance, filed lawsuits against each other over Meester's financial support of her younger brother, Alexander, who has multiple health problems.[98] Meester's suit claimed that her mother used the money she sent for "cosmetic procedures", such as botox and hair extensions. Her mother's suit made a counterclaim alleging breach of contract and physical abuse. Constance claimed that a verbal contract was in place where Meester had promised US$10,000 a month, instead of the US$7,500 she received. Her mother also claimed that she was due a larger sum in return for "sacrificing her own happiness" when she moved Meester to Los Angeles as a child to pursue acting. In court, the judge dismissed this claim. Constance accused her daughter of calling social services and fabricating a claim that she was abusing Alexander; investigators interviewed Meester and found no merit in the complaint. In November 2011, Constance dropped the US$3 million claim for damages against her daughter. Meester said that she would be willing to pay for her brother's medical expenses as well as his school tuition, but denied that she agreed to pay US$10,000 each month, which she stated was a "ridiculous" claim.[99] Meester obtained a default judgment on December 7, 2011.[100] In June 2012, Meester won the lawsuit, with the judge rejecting the claims in her mother's counter-suit.[101]

Meester resides in Los Angeles.[102] In November 2013, she became engaged to actor Adam Brody, whom she met while filming The Oranges in March 2010.[103] The couple was married in a private ceremony on February 15, 2014.[104] Their first child, daughter Arlo Day Brody, was born on August 4, 2015, in Whittier, California.[105]